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Russian Chemical Bulletin

, Volume 68, Issue 1, pp 55–63 | Cite as

Trimethyl orthoacetate as a convenient reagent for selective methylation of β-OH groups of (poly)hydroxynaphthazarins

  • N. N. Balaneva
  • O. P. ShestakEmail author
  • V. L. Novikov
Full Articles

Abstract

Trimethyl orthoacetate was found to be a convenient reagent for methylation of the β-OH groups of (poly)hydroxynaphthazarins. The substrates bearing one β-OH group react with MeC(OMe)3 to give the corresponding methoxy derivatives in 79–89% yields. Depending on the reaction conditions, methylation of substrates with two β-OH groups on the different and the same rings affords either the corresponding mono-O-methylated (43–70%) or di-Omethylated (71–78%) derivatives. Trimethyl orthoacetate offers a good alternative to CH2N2 in the preparative synthesis of O-methylated (poly)hydroxynaphthazarin derivatives.

Key words

polyhydroxy-1,4-naphthoquinones naphthazarins pigments of sea urchins naphthopurpurin mompain isomompain ethylspinazarin antioxidants O-methylation trimethyl orthoacetate 

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Copyright information

© Springer Science+Business Media, Inc. 2019

Authors and Affiliations

  • N. N. Balaneva
    • 1
  • O. P. Shestak
    • 1
    Email author
  • V. L. Novikov
    • 1
  1. 1.G. B. Elyakov Pacific Institute of Bioorganic ChemistryFar-East Branch of the Russian Academy of SciencesVladivostokRussian Federation

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